HU230061B1 - Cikloalkénszármazékok, előállításuk és alkalmazásuk - Google Patents

Info

Publication number

HU230061B1

HU230061B1 HU0101192A HUP0101192A HU230061B1 HU 230061 B1 HU230061 B1 HU 230061B1 HU 0101192 A HU0101192 A HU 0101192A HU P0101192 A HUP0101192 A HU P0101192A HU 230061 B1 HU230061 B1 HU 230061B1

Authority

HU

Hungary

Prior art keywords

group

formula

carbon atoms

carbon

alkyl

Prior art date

1998-03-09

Links

• Espacenet
• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 title claims description 53
• 230000008569 process Effects 0.000 title claims description 13
• 150000001925 cycloalkenes Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 263
• 239000000203 mixture Substances 0.000 claims description 144
• -1 graft group Chemical group 0.000 claims description 116
• 125000004432 carbon atom Chemical group C* 0.000 claims description 81
• 150000003839 salts Chemical class 0.000 claims description 68
• 239000002253 acid Substances 0.000 claims description 60
• 125000001424 substituent group Chemical group 0.000 claims description 60
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 46
• 229910052799 carbon Inorganic materials 0.000 claims description 46
• 239000000126 substance Substances 0.000 claims description 45
• 238000006243 chemical reaction Methods 0.000 claims description 42
• 239000000843 powder Substances 0.000 claims description 42
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 41
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 125000001931 aliphatic group Chemical group 0.000 claims description 29
• 125000000623 heterocyclic group Chemical group 0.000 claims description 29
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 28
• 125000003118 aryl group Chemical group 0.000 claims description 26
• 229910052717 sulfur Inorganic materials 0.000 claims description 26
• 239000001257 hydrogen Substances 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 125000004494 ethyl ester group Chemical group 0.000 claims description 21
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 125000005843 halogen group Chemical group 0.000 claims description 19
• 201000010099 disease Diseases 0.000 claims description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
• UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical group [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
• 238000004519 manufacturing process Methods 0.000 claims description 16
• 238000002360 preparation method Methods 0.000 claims description 16
• 125000004434 sulfur atom Chemical group 0.000 claims description 16
• 230000015572 biosynthetic process Effects 0.000 claims description 15
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
• 238000011282 treatment Methods 0.000 claims description 14
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 13
• 239000003921 oil Substances 0.000 claims description 13
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 206010040070 Septic Shock Diseases 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 10
• 150000001721 carbon Chemical group 0.000 claims description 10
• 239000011593 sulfur Substances 0.000 claims description 10
• 125000004043 oxo group Chemical group O=* 0.000 claims description 9
• 230000036303 septic shock Effects 0.000 claims description 9
• 206010040047 Sepsis Diseases 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 244000269722 Thea sinensis Species 0.000 claims description 7
• 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims description 7
• 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
• 239000000194 fatty acid Substances 0.000 claims description 7
• 229930195729 fatty acid Natural products 0.000 claims description 7
• 230000005764 inhibitory process Effects 0.000 claims description 7
• 229920006395 saturated elastomer Polymers 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 229940079593 drug Drugs 0.000 claims description 5
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
• 230000003647 oxidation Effects 0.000 claims description 5
• 238000007254 oxidation reaction Methods 0.000 claims description 5
• 125000004149 thio group Chemical group *S* 0.000 claims description 5
• 150000001720 carbohydrates Chemical class 0.000 claims description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 208000019622 heart disease Diseases 0.000 claims description 4
• 208000011580 syndromic disease Diseases 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 3
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
• 150000001413 amino acids Chemical class 0.000 claims description 3
• 125000000837 carbohydrate group Chemical group 0.000 claims description 3
• 239000006229 carbon black Substances 0.000 claims description 3
• 229910052742 iron Inorganic materials 0.000 claims description 3
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 230000029305 taxis Effects 0.000 claims description 3
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 2
• 239000004215 Carbon black (E152) Substances 0.000 claims description 2
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 2
• 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 2
• 241000607479 Yersinia pestis Species 0.000 claims description 2
• 125000004423 acyloxy group Chemical group 0.000 claims description 2
• 239000003513 alkali Substances 0.000 claims description 2
• 210000004556 brain Anatomy 0.000 claims description 2
• 230000003111 delayed effect Effects 0.000 claims description 2
• 235000005911 diet Nutrition 0.000 claims description 2
• 230000000378 dietary effect Effects 0.000 claims description 2
• 150000002170 ethers Chemical class 0.000 claims description 2
• 229930195733 hydrocarbon Natural products 0.000 claims description 2
• 150000002430 hydrocarbons Chemical class 0.000 claims description 2
• 239000008101 lactose Substances 0.000 claims description 2
• 231100000518 lethal Toxicity 0.000 claims description 2
• 230000001665 lethal effect Effects 0.000 claims description 2
• 230000001590 oxidative effect Effects 0.000 claims description 2
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
• 125000003710 aryl alkyl group Chemical group 0.000 claims 2
• 125000001072 heteroaryl group Chemical group 0.000 claims 2
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• XZRHNAFEYMSXRG-UHFFFAOYSA-N 2,5-dimethylbenzoic acid Chemical compound CC1=CC=C(C)C(C(O)=O)=C1 XZRHNAFEYMSXRG-UHFFFAOYSA-N 0.000 claims 1
• 241001093575 Alma Species 0.000 claims 1
• 239000005995 Aluminium silicate Substances 0.000 claims 1
• 241000195493 Cryptophyta Species 0.000 claims 1
• 239000004593 Epoxy Substances 0.000 claims 1
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 1
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 1
• FRYDSOYOHWGSMD-UHFFFAOYSA-N [C].O Chemical group [C].O FRYDSOYOHWGSMD-UHFFFAOYSA-N 0.000 claims 1
• XAQHXGSHRMHVMU-UHFFFAOYSA-N [S].[S] Chemical compound [S].[S] XAQHXGSHRMHVMU-UHFFFAOYSA-N 0.000 claims 1
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
• 125000002947 alkylene group Chemical group 0.000 claims 1
• 235000012211 aluminium silicate Nutrition 0.000 claims 1
• 125000003277 amino group Chemical group 0.000 claims 1
• 239000010426 asphalt Substances 0.000 claims 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
• 230000003816 axenic effect Effects 0.000 claims 1
• 235000015895 biscuits Nutrition 0.000 claims 1
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
• 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
• 125000002843 carboxylic acid group Chemical group 0.000 claims 1
• 150000001735 carboxylic acids Chemical class 0.000 claims 1
• 231100000433 cytotoxic Toxicity 0.000 claims 1
• 230000001472 cytotoxic effect Effects 0.000 claims 1
• 150000001983 dialkylethers Chemical class 0.000 claims 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
• 239000005556 hormone Substances 0.000 claims 1
• 229940088597 hormone Drugs 0.000 claims 1
• 235000015110 jellies Nutrition 0.000 claims 1
• 239000008274 jelly Substances 0.000 claims 1
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims 1
• 239000003607 modifier Substances 0.000 claims 1
• 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
• 235000006408 oxalic acid Nutrition 0.000 claims 1
• 239000001301 oxygen Substances 0.000 claims 1
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
• 239000008262 pumice Substances 0.000 claims 1
• 229910052710 silicon Inorganic materials 0.000 claims 1
• 239000010703 silicon Substances 0.000 claims 1
• 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
• 238000006467 substitution reaction Methods 0.000 claims 1
• 210000002435 tendon Anatomy 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 452
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 193
• 235000019439 ethyl acetate Nutrition 0.000 description 154
• 229940093499 ethyl acetate Drugs 0.000 description 147
• 238000004458 analytical method Methods 0.000 description 80
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
• 235000002639 sodium chloride Nutrition 0.000 description 68
• 239000000243 solution Substances 0.000 description 68
• 239000002904 solvent Substances 0.000 description 66
• 239000013078 crystal Substances 0.000 description 58
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
• 239000011541 reaction mixture Substances 0.000 description 51
• 238000005160 1H NMR spectroscopy Methods 0.000 description 46
• 239000000047 product Substances 0.000 description 42
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 38
• 150000002148 esters Chemical class 0.000 description 38
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
• 239000000741 silica gel Substances 0.000 description 34
• 229910002027 silica gel Inorganic materials 0.000 description 34
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
• 238000001816 cooling Methods 0.000 description 29
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 27
• 239000002585 base Substances 0.000 description 24
• 206010057190 Respiratory tract infections Diseases 0.000 description 22
• 210000004027 cell Anatomy 0.000 description 22
• 238000005481 NMR spectroscopy Methods 0.000 description 21
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 17
• 239000003480 eluent Substances 0.000 description 17
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
• 238000012360 testing method Methods 0.000 description 16
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 238000010992 reflux Methods 0.000 description 15
• 239000007787 solid Substances 0.000 description 15
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
• 239000012267 brine Substances 0.000 description 14
• 238000003756 stirring Methods 0.000 description 14
• 238000004440 column chromatography Methods 0.000 description 13
• 239000011780 sodium chloride Substances 0.000 description 13
• 235000019198 oils Nutrition 0.000 description 12
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 11
• 238000004587 chromatography analysis Methods 0.000 description 11
• 238000003818 flash chromatography Methods 0.000 description 11
• 230000002401 inhibitory effect Effects 0.000 description 11
• 230000002411 adverse Effects 0.000 description 10
• 210000004369 blood Anatomy 0.000 description 10
• 239000008280 blood Substances 0.000 description 10
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
• 238000010828 elution Methods 0.000 description 9
• 238000001704 evaporation Methods 0.000 description 9
• 239000000706 filtrate Substances 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 239000002609 medium Substances 0.000 description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• 150000004945 aromatic hydrocarbons Chemical group 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 230000008020 evaporation Effects 0.000 description 8
• 208000015181 infectious disease Diseases 0.000 description 8
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
• 150000007530 organic bases Chemical class 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
• 241001465754 Metazoa Species 0.000 description 7
• 150000001408 amides Chemical class 0.000 description 7
• 229940126214 compound 3 Drugs 0.000 description 7
• 238000002425 crystallisation Methods 0.000 description 7
• 230000008025 crystallization Effects 0.000 description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
• 235000019341 magnesium sulphate Nutrition 0.000 description 7
• 239000012071 phase Substances 0.000 description 7
• 235000013616 tea Nutrition 0.000 description 7
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
• 125000001309 chloro group Chemical group Cl* 0.000 description 6
• 150000007529 inorganic bases Chemical class 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• 238000000926 separation method Methods 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• 235000011121 sodium hydroxide Nutrition 0.000 description 6
• VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• 229940124597 therapeutic agent Drugs 0.000 description 6
• 102000004127 Cytokines Human genes 0.000 description 5
• 108090000695 Cytokines Proteins 0.000 description 5
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
• 229920002472 Starch Polymers 0.000 description 5
• 230000001154 acute effect Effects 0.000 description 5
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 5
• 229910052801 chlorine Inorganic materials 0.000 description 5
• 229940125904 compound 1 Drugs 0.000 description 5
• 239000003085 diluting agent Substances 0.000 description 5
• 150000004665 fatty acids Chemical class 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
• 229910017604 nitric acid Inorganic materials 0.000 description 5
• 239000008188 pellet Substances 0.000 description 5
• 239000008107 starch Substances 0.000 description 5
• 235000019698 starch Nutrition 0.000 description 5
• 229940086542 triethylamine Drugs 0.000 description 5
• 240000003291 Armoracia rusticana Species 0.000 description 4
• 235000011330 Armoracia rusticana Nutrition 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
• 206010028980 Neoplasm Diseases 0.000 description 4
• 102100029438 Nitric oxide synthase, inducible Human genes 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 229910000831 Steel Inorganic materials 0.000 description 4
• 102100040247 Tumor necrosis factor Human genes 0.000 description 4
• LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 4
• 239000000654 additive Substances 0.000 description 4
• 230000000996 additive effect Effects 0.000 description 4
• 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 4
• 239000008346 aqueous phase Substances 0.000 description 4
• 239000007864 aqueous solution Substances 0.000 description 4
• 230000001580 bacterial effect Effects 0.000 description 4
• 208000015114 central nervous system disease Diseases 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 229940127204 compound 29 Drugs 0.000 description 4
• 230000002500 effect on skin Effects 0.000 description 4
• 239000000499 gel Substances 0.000 description 4
• 150000002431 hydrogen Chemical class 0.000 description 4
• 208000027866 inflammatory disease Diseases 0.000 description 4
• 239000011777 magnesium Substances 0.000 description 4
• 229910052749 magnesium Inorganic materials 0.000 description 4
• 210000002569 neuron Anatomy 0.000 description 4
• 150000007524 organic acids Chemical class 0.000 description 4
• 125000004430 oxygen atom Chemical group O* 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
• 239000011347 resin Substances 0.000 description 4
• 229920005989 resin Polymers 0.000 description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 description 4
• 238000010898 silica gel chromatography Methods 0.000 description 4
• 239000010959 steel Substances 0.000 description 4
• 239000000829 suppository Substances 0.000 description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• 150000004685 tetrahydrates Chemical class 0.000 description 4
• 238000005406 washing Methods 0.000 description 4
• MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 3
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 3
• 208000035473 Communicable disease Diseases 0.000 description 3
• 208000005189 Embolism Diseases 0.000 description 3
• 102000008070 Interferon-gamma Human genes 0.000 description 3
• 108010074328 Interferon-gamma Proteins 0.000 description 3
• 241000124008 Mammalia Species 0.000 description 3
• 241000699670 Mus sp. Species 0.000 description 3
• 229910002651 NO3 Inorganic materials 0.000 description 3
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 3
• 230000002378 acidificating effect Effects 0.000 description 3
• 229910052783 alkali metal Inorganic materials 0.000 description 3
• 125000003342 alkenyl group Chemical group 0.000 description 3
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
• 208000007502 anemia Diseases 0.000 description 3
• 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
• 125000005129 aryl carbonyl group Chemical group 0.000 description 3
• 125000001246 bromo group Chemical group Br* 0.000 description 3
• 201000011510 cancer Diseases 0.000 description 3
• 239000001913 cellulose Substances 0.000 description 3
• 229920002678 cellulose Polymers 0.000 description 3
• 239000000460 chlorine Substances 0.000 description 3
• 230000001684 chronic effect Effects 0.000 description 3
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 3
• 206010012601 diabetes mellitus Diseases 0.000 description 3
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
• 239000007789 gas Substances 0.000 description 3
• 238000001727 in vivo Methods 0.000 description 3
• 230000001939 inductive effect Effects 0.000 description 3
• 230000002757 inflammatory effect Effects 0.000 description 3
• 229960003130 interferon gamma Drugs 0.000 description 3
• 238000002955 isolation Methods 0.000 description 3
• 229910052744 lithium Inorganic materials 0.000 description 3
• 239000000314 lubricant Substances 0.000 description 3
• 210000002540 macrophage Anatomy 0.000 description 3
• 150000007522 mineralic acids Chemical class 0.000 description 3
• 230000003287 optical effect Effects 0.000 description 3
• 201000008482 osteoarthritis Diseases 0.000 description 3
• 125000002971 oxazolyl group Chemical group 0.000 description 3
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
• 229910052698 phosphorus Inorganic materials 0.000 description 3
• 239000011574 phosphorus Substances 0.000 description 3
• 239000011591 potassium Substances 0.000 description 3
• 229910052700 potassium Inorganic materials 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• 230000000069 prophylactic effect Effects 0.000 description 3
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
• 230000035939 shock Effects 0.000 description 3
• 239000004317 sodium nitrate Substances 0.000 description 3
• 235000010344 sodium nitrate Nutrition 0.000 description 3
• 159000000000 sodium salts Chemical class 0.000 description 3
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
• 210000005166 vasculature Anatomy 0.000 description 3
• 239000003981 vehicle Substances 0.000 description 3
• IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 2
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
• WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 2
• SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
• SIIGGFCBVDNNNU-UHFFFAOYSA-N 2-ethoxycarbonylcyclohexene-1-sulfonic acid Chemical compound CCOC(=O)C1=C(S(O)(=O)=O)CCCC1 SIIGGFCBVDNNNU-UHFFFAOYSA-N 0.000 description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
• XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 2
• RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
• 102000011767 Acute-Phase Proteins Human genes 0.000 description 2
• 108010062271 Acute-Phase Proteins Proteins 0.000 description 2
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
• 208000023275 Autoimmune disease Diseases 0.000 description 2
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
• 208000031229 Cardiomyopathies Diseases 0.000 description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
• 206010012735 Diarrhoea Diseases 0.000 description 2
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
• 239000001856 Ethyl cellulose Substances 0.000 description 2
• ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• 239000005977 Ethylene Substances 0.000 description 2
• AIKKULXCBHRFOS-UHFFFAOYSA-N Formothion Chemical group COP(=S)(OC)SCC(=O)N(C)C=O AIKKULXCBHRFOS-UHFFFAOYSA-N 0.000 description 2
• 206010019280 Heart failures Diseases 0.000 description 2
• 241000282414 Homo sapiens Species 0.000 description 2
• 206010020772 Hypertension Diseases 0.000 description 2
• 206010020843 Hyperthermia Diseases 0.000 description 2
• 108010002352 Interleukin-1 Proteins 0.000 description 2
• 241001435619 Lile Species 0.000 description 2
• 208000019693 Lung disease Diseases 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
• 108010076864 Nitric Oxide Synthase Type II Proteins 0.000 description 2
• 102100028452 Nitric oxide synthase, endothelial Human genes 0.000 description 2
• 101710090055 Nitric oxide synthase, endothelial Proteins 0.000 description 2
• 101710089543 Nitric oxide synthase, inducible Proteins 0.000 description 2
• 208000001132 Osteoporosis Diseases 0.000 description 2
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
• 201000004681 Psoriasis Diseases 0.000 description 2
• 208000001647 Renal Insufficiency Diseases 0.000 description 2
• 208000007107 Stomach Ulcer Diseases 0.000 description 2
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
• 125000005236 alkanoylamino group Chemical group 0.000 description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
• 125000000304 alkynyl group Chemical group 0.000 description 2
• 235000001014 amino acid Nutrition 0.000 description 2
• 150000003863 ammonium salts Chemical class 0.000 description 2
• 238000010171 animal model Methods 0.000 description 2
• 230000003110 anti-inflammatory effect Effects 0.000 description 2
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 2
• 125000004104 aryloxy group Chemical group 0.000 description 2
• 230000001363 autoimmune Effects 0.000 description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
• 229910052794 bromium Inorganic materials 0.000 description 2
• 239000011575 calcium Substances 0.000 description 2
• 229910052791 calcium Inorganic materials 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
• 239000003153 chemical reaction reagent Substances 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• 239000011248 coating agent Substances 0.000 description 2
• 238000000576 coating method Methods 0.000 description 2
• 229940125807 compound 37 Drugs 0.000 description 2
• 239000012141 concentrate Substances 0.000 description 2
• 235000012343 cottonseed oil Nutrition 0.000 description 2
• 239000002385 cottonseed oil Substances 0.000 description 2
• 239000012228 culture supernatant Substances 0.000 description 2
• 125000005366 cycloalkylthio group Chemical group 0.000 description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
• 239000002552 dosage form Substances 0.000 description 2
• 239000000428 dust Substances 0.000 description 2
• 206010015037 epilepsy Diseases 0.000 description 2
• GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 2
• 229920001249 ethyl cellulose Polymers 0.000 description 2
• 235000019325 ethyl cellulose Nutrition 0.000 description 2
• 230000001605 fetal effect Effects 0.000 description 2
• 229910052731 fluorine Inorganic materials 0.000 description 2
• 239000011737 fluorine Substances 0.000 description 2
• 125000001153 fluoro group Chemical group F* 0.000 description 2
• 125000001207 fluorophenyl group Chemical group 0.000 description 2
• 230000000762 glandular Effects 0.000 description 2
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
• 230000036031 hyperthermia Effects 0.000 description 2
• 230000001965 increasing effect Effects 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 229910010272 inorganic material Inorganic materials 0.000 description 2
• 239000011147 inorganic material Substances 0.000 description 2
• 239000000543 intermediate Substances 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• 125000000842 isoxazolyl group Chemical group 0.000 description 2
• 208000017169 kidney disease Diseases 0.000 description 2
• 201000006370 kidney failure Diseases 0.000 description 2
• 210000004698 lymphocyte Anatomy 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
• 239000011976 maleic acid Substances 0.000 description 2
• BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical group OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
• 239000000463 material Substances 0.000 description 2
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
• 150000004702 methyl esters Chemical class 0.000 description 2
• 235000013336 milk Nutrition 0.000 description 2
• 239000008267 milk Substances 0.000 description 2
• 210000004080 milk Anatomy 0.000 description 2
• 239000012046 mixed solvent Substances 0.000 description 2
• 239000012452 mother liquor Substances 0.000 description 2
• 208000010125 myocardial infarction Diseases 0.000 description 2
• 238000006386 neutralization reaction Methods 0.000 description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
• 239000000546 pharmaceutical excipient Substances 0.000 description 2
• MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• 239000002243 precursor Substances 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• 230000035484 reaction time Effects 0.000 description 2
• 102000005962 receptors Human genes 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 230000002829 reductive effect Effects 0.000 description 2
• 230000001105 regulatory effect Effects 0.000 description 2
• 102220044643 rs587781450 Human genes 0.000 description 2
• 201000000980 schizophrenia Diseases 0.000 description 2
• 210000002966 serum Anatomy 0.000 description 2
• 239000008159 sesame oil Substances 0.000 description 2
• 235000011803 sesame oil Nutrition 0.000 description 2
• 239000002893 slag Substances 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• 230000000638 stimulation Effects 0.000 description 2
• 239000004094 surface-active agent Substances 0.000 description 2
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
• 210000001519 tissue Anatomy 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
• FHYUCVWDMABHHH-UHFFFAOYSA-N toluene;1,2-xylene Chemical group CC1=CC=CC=C1.CC1=CC=CC=C1C FHYUCVWDMABHHH-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• 230000002792 vascular Effects 0.000 description 2
• 235000015112 vegetable and seed oil Nutrition 0.000 description 2
• 239000008158 vegetable oil Substances 0.000 description 2
• XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 1
• ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
• GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 1
• YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
• STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
• FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 description 1
• MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
• STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
• MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
• 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
• KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 1
• KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
• WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
• QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 1
• NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 1
• SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
• AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
• JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 1
• PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
• TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
• HKHXLHGVIHQKMK-UHFFFAOYSA-N 2-chloro-m-cresol Chemical compound CC1=CC=CC(O)=C1Cl HKHXLHGVIHQKMK-UHFFFAOYSA-N 0.000 description 1
• RVBUZBPJAGZHSQ-UHFFFAOYSA-N 2-chlorobutanoic acid Chemical compound CCC(Cl)C(O)=O RVBUZBPJAGZHSQ-UHFFFAOYSA-N 0.000 description 1
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
• YURNCBVQZBJDAJ-UHFFFAOYSA-N 2-heptenoic acid Chemical compound CCCCC=CC(O)=O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 description 1
• RMGHERXMTMUMMV-UHFFFAOYSA-N 2-methoxypropane Chemical compound COC(C)C RMGHERXMTMUMMV-UHFFFAOYSA-N 0.000 description 1
• 125000005975 2-phenylethyloxy group Chemical group 0.000 description 1
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
• WHNQTHDJEZTVHS-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)propanoic acid Chemical compound C1=CC=C2SC(CCC(=O)O)=NC2=C1 WHNQTHDJEZTVHS-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 1
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
• JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
• SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 1
• GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 1
• WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• 125000005330 8 membered heterocyclic group Chemical group 0.000 description 1
• 235000004507 Abies alba Nutrition 0.000 description 1
• 244000178606 Abies grandis Species 0.000 description 1
• 235000017894 Abies grandis Nutrition 0.000 description 1
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
• 208000002874 Acne Vulgaris Diseases 0.000 description 1
• 206010000830 Acute leukaemia Diseases 0.000 description 1
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
• 229920001817 Agar Polymers 0.000 description 1
• 241001279686 Allium moly Species 0.000 description 1
• 101150043850 Amtn gene Proteins 0.000 description 1
• 206010002383 Angina Pectoris Diseases 0.000 description 1
• 206010002388 Angina unstable Diseases 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 235000009581 Balanites aegyptiaca Nutrition 0.000 description 1
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
• 208000014644 Brain disease Diseases 0.000 description 1
• 240000007124 Brassica oleracea Species 0.000 description 1
• 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
• 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
• 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
• 206010006187 Breast cancer Diseases 0.000 description 1
• 208000026310 Breast neoplasm Diseases 0.000 description 1
• 241001609030 Brosme brosme Species 0.000 description 1
• HCVANKFEUQUUGJ-UHFFFAOYSA-N C(=O)(Cl)Cl.[C] Chemical group C(=O)(Cl)Cl.[C] HCVANKFEUQUUGJ-UHFFFAOYSA-N 0.000 description 1
• 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
• 101150043532 CISH gene Proteins 0.000 description 1
• PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 1
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
• 244000025254 Cannabis sativa Species 0.000 description 1
• 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
• 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
• 241000283707 Capra Species 0.000 description 1
• 229920000049 Carbon (fiber) Polymers 0.000 description 1
• 102100025064 Cellular tumor antigen p53 Human genes 0.000 description 1
• 206010009900 Colitis ulcerative Diseases 0.000 description 1
• 206010009944 Colon cancer Diseases 0.000 description 1
• 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
• 206010011469 Crying Diseases 0.000 description 1
• GVOUFPWUYJWQSK-UHFFFAOYSA-N Cyclofenil Chemical group C1=CC(OC(=O)C)=CC=C1C(C=1C=CC(OC(C)=O)=CC=1)=C1CCCCC1 GVOUFPWUYJWQSK-UHFFFAOYSA-N 0.000 description 1
• 241000252233 Cyprinus carpio Species 0.000 description 1
• 101100193633 Danio rerio rag2 gene Proteins 0.000 description 1
• 208000019505 Deglutition disease Diseases 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical compound CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 1
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
• LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• 206010015150 Erythema Diseases 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
• 206010017076 Fracture Diseases 0.000 description 1
• 241000237858 Gastropoda Species 0.000 description 1
• 244000068988 Glycine max Species 0.000 description 1
• 235000010469 Glycine max Nutrition 0.000 description 1
• 201000005569 Gout Diseases 0.000 description 1
• 206010019663 Hepatic failure Diseases 0.000 description 1
• 208000004898 Herpes Labialis Diseases 0.000 description 1
• 208000007514 Herpes zoster Diseases 0.000 description 1
• 101000721661 Homo sapiens Cellular tumor antigen p53 Proteins 0.000 description 1
• 241000725303 Human immunodeficiency virus Species 0.000 description 1
• 241000701806 Human papillomavirus Species 0.000 description 1
• 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
• XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
• 206010061218 Inflammation Diseases 0.000 description 1
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
• 108010002350 Interleukin-2 Proteins 0.000 description 1
• 108090000978 Interleukin-4 Proteins 0.000 description 1
• 108090001005 Interleukin-6 Proteins 0.000 description 1
• 108090001007 Interleukin-8 Proteins 0.000 description 1
• 201000001429 Intracranial Thrombosis Diseases 0.000 description 1
• 208000032382 Ischaemic stroke Diseases 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N L-glucitol Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• 239000004166 Lanolin Substances 0.000 description 1
• 241000270322 Lepidosauria Species 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 102000003960 Ligases Human genes 0.000 description 1
• 108090000364 Ligases Proteins 0.000 description 1
• 240000006240 Linum usitatissimum Species 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 229910021407 M-carbon Inorganic materials 0.000 description 1
• 241000282553 Macaca Species 0.000 description 1
• 201000009906 Meningitis Diseases 0.000 description 1
• 206010027476 Metastases Diseases 0.000 description 1
• 241000699666 Mus <mouse, genus> Species 0.000 description 1
• 101100227720 Mus musculus Frk gene Proteins 0.000 description 1
• 101100193635 Mus musculus Rag2 gene Proteins 0.000 description 1
• 208000023178 Musculoskeletal disease Diseases 0.000 description 1
• HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
• OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
• IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
• 206010029897 Obsessive thoughts Diseases 0.000 description 1
• 206010067152 Oral herpes Diseases 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• 241000237502 Ostreidae Species 0.000 description 1
• 206010033128 Ovarian cancer Diseases 0.000 description 1
• 206010061535 Ovarian neoplasm Diseases 0.000 description 1
• 102000004020 Oxygenases Human genes 0.000 description 1
• 108090000417 Oxygenases Proteins 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 229930012538 Paclitaxel Natural products 0.000 description 1
• 208000018737 Parkinson disease Diseases 0.000 description 1
• 208000008469 Peptic Ulcer Diseases 0.000 description 1
• 108091005804 Peptidases Proteins 0.000 description 1
• 241000009328 Perro Species 0.000 description 1
• RZKYEQDPDZUERB-UHFFFAOYSA-N Pindone Chemical compound C1=CC=C2C(=O)C(C(=O)C(C)(C)C)C(=O)C2=C1 RZKYEQDPDZUERB-UHFFFAOYSA-N 0.000 description 1
• 240000004713 Pisum sativum Species 0.000 description 1
• 235000010582 Pisum sativum Nutrition 0.000 description 1
• 206010035226 Plasma cell myeloma Diseases 0.000 description 1
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 206010060862 Prostate cancer Diseases 0.000 description 1
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
• 239000004365 Protease Substances 0.000 description 1
• 102000001708 Protein Isoforms Human genes 0.000 description 1
• 108010029485 Protein Isoforms Proteins 0.000 description 1
• 206010037660 Pyrexia Diseases 0.000 description 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
• 244000088415 Raphanus sativus Species 0.000 description 1
• 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
• 208000035977 Rare disease Diseases 0.000 description 1
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
• 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
• 206010039085 Rhinitis allergic Diseases 0.000 description 1
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
• 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
• 206010041067 Small cell lung cancer Diseases 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• 208000005718 Stomach Neoplasms Diseases 0.000 description 1
• 208000006011 Stroke Diseases 0.000 description 1
• 229920006328 Styrofoam Polymers 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
• 206010042496 Sunburn Diseases 0.000 description 1
• 206010042618 Surgical procedure repeated Diseases 0.000 description 1
• 240000000278 Syzygium polyanthum Species 0.000 description 1
• 241000375392 Tana Species 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 241000718541 Tetragastris balsamifera Species 0.000 description 1
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
• 241000219793 Trifolium Species 0.000 description 1
• 108010040002 Tumor Suppressor Proteins Proteins 0.000 description 1
• 102000001742 Tumor Suppressor Proteins Human genes 0.000 description 1
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
• 208000025865 Ulcer Diseases 0.000 description 1
• 201000006704 Ulcerative Colitis Diseases 0.000 description 1
• 208000007814 Unstable Angina Diseases 0.000 description 1
• 208000006593 Urologic Neoplasms Diseases 0.000 description 1
• 206010046996 Varicose vein Diseases 0.000 description 1
• 241000700605 Viruses Species 0.000 description 1
• 208000027418 Wounds and injury Diseases 0.000 description 1
• LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
• JXBAVRIYDKLCOE-UHFFFAOYSA-N [C].[P] Chemical group [C].[P] JXBAVRIYDKLCOE-UHFFFAOYSA-N 0.000 description 1
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 1
• 150000008043 acidic salts Chemical class 0.000 description 1
• 206010000496 acne Diseases 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 230000004913 activation Effects 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 201000010275 acute porphyria Diseases 0.000 description 1
• 239000008272 agar Substances 0.000 description 1
• 230000032683 aging Effects 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical group CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 125000000033 alkoxyamino group Chemical group 0.000 description 1
• 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
• 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
• 125000006177 alkyl benzyl group Chemical group 0.000 description 1
• 125000005907 alkyl ester group Chemical group 0.000 description 1
• 125000004414 alkyl thio group Chemical group 0.000 description 1
• 125000005133 alkynyloxy group Chemical group 0.000 description 1
• 208000026935 allergic disease Diseases 0.000 description 1
• 201000010105 allergic rhinitis Diseases 0.000 description 1
• QUMXDOLUJCHOAY-UHFFFAOYSA-N alpha-methylbenzyl acetate Natural products CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 150000008064 anhydrides Chemical class 0.000 description 1
• 230000001093 anti-cancer Effects 0.000 description 1
• 239000002260 anti-inflammatory agent Substances 0.000 description 1
• 229940121363 anti-inflammatory agent Drugs 0.000 description 1
• 239000007900 aqueous suspension Substances 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 206010003119 arrhythmia Diseases 0.000 description 1
• 150000005840 aryl radicals Chemical class 0.000 description 1
• 125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 1
• 235000003704 aspartic acid Nutrition 0.000 description 1
• 229910052789 astatine Inorganic materials 0.000 description 1
• XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
• 229910000063 azene Inorganic materials 0.000 description 1
• RQVGAIADHNPSME-UHFFFAOYSA-N azinphos-ethyl Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OCC)OCC)N=NC2=C1 RQVGAIADHNPSME-UHFFFAOYSA-N 0.000 description 1
• 244000052616 bacterial pathogen Species 0.000 description 1
• 230000004888 barrier function Effects 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• 125000005605 benzo group Chemical group 0.000 description 1
• XIWFQDBQMCDYJT-UHFFFAOYSA-M benzyl-dimethyl-tridecylazanium;chloride Chemical group [Cl-].CCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 XIWFQDBQMCDYJT-UHFFFAOYSA-M 0.000 description 1
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 239000004305 biphenyl Substances 0.000 description 1
• 235000010290 biphenyl Nutrition 0.000 description 1
• 230000000903 blocking effect Effects 0.000 description 1
• 230000036765 blood level Effects 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 229910021538 borax Inorganic materials 0.000 description 1
• 229910052796 boron Inorganic materials 0.000 description 1
• 125000000707 boryl group Chemical group B* 0.000 description 1
• 210000000481 breast Anatomy 0.000 description 1
• 230000005587 bubbling Effects 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000004364 calculation method Methods 0.000 description 1
• 244000309466 calf Species 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
• 239000004917 carbon fiber Substances 0.000 description 1
• FTAHXGPNHBWWDP-UHFFFAOYSA-N carbon monoxide Chemical compound [O+]#[C-].[O+]#[C-] FTAHXGPNHBWWDP-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 125000005102 carbonylalkoxy group Chemical group 0.000 description 1
• JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
• 125000004181 carboxyalkyl group Chemical group 0.000 description 1
• 230000000747 cardiac effect Effects 0.000 description 1
• 206010061592 cardiac fibrillation Diseases 0.000 description 1
• 239000006285 cell suspension Substances 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 230000003727 cerebral blood flow Effects 0.000 description 1
• 206010008129 cerebral palsy Diseases 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• 230000004087 circulation Effects 0.000 description 1
• 239000007979 citrate buffer Substances 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 230000015271 coagulation Effects 0.000 description 1
• 238000005345 coagulation Methods 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 239000012230 colorless oil Substances 0.000 description 1
• 229940125797 compound 12 Drugs 0.000 description 1
• 229940126086 compound 21 Drugs 0.000 description 1
• 229940125961 compound 24 Drugs 0.000 description 1
• 229940125851 compound 27 Drugs 0.000 description 1
• 229940125877 compound 31 Drugs 0.000 description 1
• 229940125878 compound 36 Drugs 0.000 description 1
• 229940127573 compound 38 Drugs 0.000 description 1
• 229940125900 compound 59 Drugs 0.000 description 1
• 229940126179 compound 72 Drugs 0.000 description 1
• JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
• 235000005687 corn oil Nutrition 0.000 description 1
• 239000002285 corn oil Substances 0.000 description 1
• 238000005859 coupling reaction Methods 0.000 description 1
• 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 1
• 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 description 1
• 229960002944 cyclofenil Drugs 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 210000004292 cytoskeleton Anatomy 0.000 description 1
• 230000008260 defense mechanism Effects 0.000 description 1
• 230000007812 deficiency Effects 0.000 description 1
• 229940120124 dichloroacetate Drugs 0.000 description 1
• NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
• 230000004069 differentiation Effects 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
• 125000000532 dioxanyl group Chemical group 0.000 description 1
• POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• CDMADVZSLOHIFP-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane;decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 CDMADVZSLOHIFP-UHFFFAOYSA-N 0.000 description 1
• 238000006073 displacement reaction Methods 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 210000001198 duodenum Anatomy 0.000 description 1
• 238000004043 dyeing Methods 0.000 description 1
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 210000000750 endocrine system Anatomy 0.000 description 1
• 210000002889 endothelial cell Anatomy 0.000 description 1
• BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• 208000001780 epistaxis Diseases 0.000 description 1
• 230000003628 erosive effect Effects 0.000 description 1
• 231100000321 erythema Toxicity 0.000 description 1
• 239000012374 esterification agent Substances 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 1
• HDKVSEUEUWKMFS-UHFFFAOYSA-N ethyl cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1 HDKVSEUEUWKMFS-UHFFFAOYSA-N 0.000 description 1
• LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
• 229940093471 ethyl oleate Drugs 0.000 description 1
• FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
• 230000005284 excitation Effects 0.000 description 1
• 239000000284 extract Substances 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• 230000004720 fertilization Effects 0.000 description 1
• 230000002600 fibrillogenic effect Effects 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 235000019634 flavors Nutrition 0.000 description 1
• 239000012530 fluid Substances 0.000 description 1
• 235000013305 food Nutrition 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
• 238000010575 fractional recrystallization Methods 0.000 description 1
• 239000012634 fragment Substances 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 206010017758 gastric cancer Diseases 0.000 description 1
• 201000005917 gastric ulcer Diseases 0.000 description 1
• 230000001434 glomerular Effects 0.000 description 1
• PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
• 229910052737 gold Inorganic materials 0.000 description 1
• 239000010931 gold Substances 0.000 description 1
• 230000005484 gravity Effects 0.000 description 1
• 244000144993 groups of animals Species 0.000 description 1
• 239000001963 growth medium Substances 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 125000004438 haloalkoxy group Chemical group 0.000 description 1
• 150000008282 halocarbons Chemical class 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 210000000777 hematopoietic system Anatomy 0.000 description 1
• 208000014617 hemorrhoid Diseases 0.000 description 1
• 208000033552 hepatic porphyria Diseases 0.000 description 1
• MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
• 125000004404 heteroalkyl group Chemical group 0.000 description 1
• 125000005842 heteroatom Chemical group 0.000 description 1
• 238000004128 high performance liquid chromatography Methods 0.000 description 1
• 210000003630 histaminocyte Anatomy 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 150000004678 hydrides Chemical class 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 230000002209 hydrophobic effect Effects 0.000 description 1
• 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
• 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
• 206010020718 hyperplasia Diseases 0.000 description 1
• 201000004108 hypersplenism Diseases 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• MPNFTLVUPHPSOV-UHFFFAOYSA-N imino(dimethyl)-$l^{4}-sulfane Chemical compound CS(C)=N MPNFTLVUPHPSOV-UHFFFAOYSA-N 0.000 description 1
• 230000009390 immune abnormality Effects 0.000 description 1
• 230000006872 improvement Effects 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 230000006698 induction Effects 0.000 description 1
• 230000002458 infectious effect Effects 0.000 description 1
• 208000021267 infertility disease Diseases 0.000 description 1
• 210000004969 inflammatory cell Anatomy 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 206010022000 influenza Diseases 0.000 description 1
• 230000000977 initiatory effect Effects 0.000 description 1
• 206010022437 insomnia Diseases 0.000 description 1
• 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
• 230000000968 intestinal effect Effects 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• 230000000622 irritating effect Effects 0.000 description 1
• 230000000302 ischemic effect Effects 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 229940039717 lanolin Drugs 0.000 description 1
• 235000019388 lanolin Nutrition 0.000 description 1
• 208000032839 leukemia Diseases 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 208000007903 liver failure Diseases 0.000 description 1
• 231100000835 liver failure Toxicity 0.000 description 1
• 230000001926 lymphatic effect Effects 0.000 description 1
• 210000004324 lymphatic system Anatomy 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 201000004792 malaria Diseases 0.000 description 1
• 229940049920 malate Drugs 0.000 description 1
• 230000036244 malformation Effects 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 230000003211 malignant effect Effects 0.000 description 1
• 230000000873 masking effect Effects 0.000 description 1
• 239000011159 matrix material Substances 0.000 description 1
• 235000012054 meals Nutrition 0.000 description 1
• 201000001441 melanoma Diseases 0.000 description 1
• 229910052753 mercury Inorganic materials 0.000 description 1
• 230000001394 metastastic effect Effects 0.000 description 1
• 206010061289 metastatic neoplasm Diseases 0.000 description 1
• 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
• MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
• 239000003595 mist Substances 0.000 description 1
• 238000012544 monitoring process Methods 0.000 description 1
• 230000002969 morbid Effects 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• 210000003205 muscle Anatomy 0.000 description 1
• 201000000050 myeloid neoplasm Diseases 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 229920001206 natural gum Polymers 0.000 description 1
• 210000000822 natural killer cell Anatomy 0.000 description 1
• IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
• 210000005036 nerve Anatomy 0.000 description 1
• 210000000653 nervous system Anatomy 0.000 description 1
• 210000000440 neutrophil Anatomy 0.000 description 1
• 229910052759 nickel Inorganic materials 0.000 description 1
• 150000002815 nickel Chemical group 0.000 description 1
• 238000006396 nitration reaction Methods 0.000 description 1
• 150000004767 nitrides Chemical class 0.000 description 1
• 150000002825 nitriles Chemical class 0.000 description 1
• JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 description 1
• 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
• 239000004006 olive oil Substances 0.000 description 1
• 235000008390 olive oil Nutrition 0.000 description 1
• PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 208000038009 orphan disease Diseases 0.000 description 1
• 125000005188 oxoalkyl group Chemical group 0.000 description 1
• QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
• 235000020636 oyster Nutrition 0.000 description 1
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
• 229960001592 paclitaxel Drugs 0.000 description 1
• 239000003973 paint Substances 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 230000036961 partial effect Effects 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 230000001175 peptic effect Effects 0.000 description 1
• 208000011906 peptic ulcer disease Diseases 0.000 description 1
• 230000002085 persistent effect Effects 0.000 description 1
• 235000019271 petrolatum Nutrition 0.000 description 1
• 239000000825 pharmaceutical preparation Substances 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 150000002989 phenols Chemical class 0.000 description 1
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
• CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical class OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• DCWXELXMIBXGTH-UHFFFAOYSA-N phosphotyrosine Chemical compound OC(=O)C(N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-UHFFFAOYSA-N 0.000 description 1
• 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
• 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
• 230000035479 physiological effects, processes and functions Effects 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 102000040430 polynucleotide Human genes 0.000 description 1
• 108091033319 polynucleotide Proteins 0.000 description 1
• 239000002157 polynucleotide Substances 0.000 description 1
• 229920001282 polysaccharide Polymers 0.000 description 1
• 239000005017 polysaccharide Substances 0.000 description 1
• 150000004804 polysaccharides Chemical class 0.000 description 1
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
• 230000003449 preventive effect Effects 0.000 description 1
• 108090000765 processed proteins & peptides Proteins 0.000 description 1
• 230000000770 proinflammatory effect Effects 0.000 description 1
• 239000001294 propane Substances 0.000 description 1
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
• 229940080818 propionamide Drugs 0.000 description 1
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 230000009979 protective mechanism Effects 0.000 description 1
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 230000001698 pyrogenic effect Effects 0.000 description 1
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
• 230000005855 radiation Effects 0.000 description 1
• 150000003254 radicals Chemical class 0.000 description 1
• 238000002271 resection Methods 0.000 description 1
• 206010039083 rhinitis Diseases 0.000 description 1
• 238000006798 ring closing metathesis reaction Methods 0.000 description 1
• 238000007363 ring formation reaction Methods 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 239000012266 salt solution Substances 0.000 description 1
• 229910052594 sapphire Inorganic materials 0.000 description 1
• 239000010980 sapphire Substances 0.000 description 1
• 230000002000 scavenging effect Effects 0.000 description 1
• 238000007789 sealing Methods 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 208000013223 septicemia Diseases 0.000 description 1
• 238000013207 serial dilution Methods 0.000 description 1
• 210000003491 skin Anatomy 0.000 description 1
• 239000002002 slurry Substances 0.000 description 1
• 208000000587 small cell lung carcinoma Diseases 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229910000104 sodium hydride Inorganic materials 0.000 description 1
• 235000010339 sodium tetraborate Nutrition 0.000 description 1
• 239000008279 sol Substances 0.000 description 1
• 238000000638 solvent extraction Methods 0.000 description 1
• 239000011877 solvent mixture Substances 0.000 description 1
• 239000003549 soybean oil Substances 0.000 description 1
• 235000012424 soybean oil Nutrition 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 238000004544 sputter deposition Methods 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 230000003068 static effect Effects 0.000 description 1
• 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000003351 stiffener Substances 0.000 description 1
• 201000011549 stomach cancer Diseases 0.000 description 1
• 230000035882 stress Effects 0.000 description 1
• 239000008261 styrofoam Substances 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
• 229910021653 sulphate ion Inorganic materials 0.000 description 1
• 239000006228 supernatant Substances 0.000 description 1
• 239000013589 supplement Substances 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 230000002194 synthesizing effect Effects 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 206010052366 systemic mycosis Diseases 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
• SJMDMGHPMLKLHQ-UHFFFAOYSA-N tert-butyl 2-aminoacetate Chemical compound CC(C)(C)OC(=O)CN SJMDMGHPMLKLHQ-UHFFFAOYSA-N 0.000 description 1
• YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
• 210000001550 testis Anatomy 0.000 description 1
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• CFMYXEVWODSLAX-QOZOJKKESA-N tetrodotoxin Chemical compound O([C@@]([C@H]1O)(O)O[C@H]2[C@@]3(O)CO)[C@H]3[C@@H](O)[C@]11[C@H]2[C@@H](O)N=C(N)N1 CFMYXEVWODSLAX-QOZOJKKESA-N 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 238000004809 thin layer chromatography Methods 0.000 description 1
• 210000001541 thymus gland Anatomy 0.000 description 1
• 239000004408 titanium dioxide Substances 0.000 description 1
• 125000004360 trifluorophenyl group Chemical group 0.000 description 1
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
• 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
• 230000002485 urinary effect Effects 0.000 description 1
• 238000007738 vacuum evaporation Methods 0.000 description 1
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 208000027185 varicose disease Diseases 0.000 description 1
• 230000009385 viral infection Effects 0.000 description 1
• 230000003612 virological effect Effects 0.000 description 1
• 239000002023 wood Substances 0.000 description 1
• 238000010626 work up procedure Methods 0.000 description 1
• 229920001221 xylan Polymers 0.000 description 1
• 150000004823 xylans Chemical class 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1